Organic Chemistry
Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 23, Problem 23.59AP
Interpretation Introduction

(a)

Interpretation:

An explanation as to why the barrier to the internal rotation about N- phenyl bond in N- methyl -p- nitroaniline is considerably higher than that in N- methylaniline itself is to be stated.

Concept introduction:

Intermolecular forces are considered as the forces that exist between the atomic moiety carrying dissimilar charges or partial difference in the charges as in the case of dipoles (atoms carrying partial positive and negative charges) and in those which contain hydrogen bonding.

The term, intramolecular hydrogen bonding is used when the hydrogen bonding occurs between two or more molecules.

Interpretation Introduction

(b)

Interpretation:

An explanation as to why cis-and trans-1, 3- dimethylpyrrolidine rapidly interconvert is to be stated.

Concept introduction:

Isomers are the compounds sharing same molecular formula but differ in the arrangements of atoms and molecules. The stereoisomer is two or more compounds that differ in the spatial arrangement of the atoms. The cis-and trans-isomersim is also known as geometrical isomerism.

Interpretation Introduction

(c)

Interpretation:

An explanation as to why CH3NHCH2NHCH3 is unstable in aqueous solution is to be stated.

Concept introduction:

The nucleophilic substitution reactions are the reactions in which one nucleophile is substituted by another nucleophile. These reactions depend upon the nucleophilicity and concentration of the nucleophile. The SN1 reaction is a nucleophilic substitution reaction in which the substitution of nucleophile takes place. This reaction takes place in two steps. There is generation of carbocation in the first step and in the second step the nucleophile attacks at the carbocation for the corresponding product.

Interpretation Introduction

(d)

Interpretation:

An explanation as to why given compound exist as the enamine isomer rather than an imine is to be stated.

Concept introduction:

Isomers are the compounds sharing same molecular formula but differ in the arrangements of atoms and molecules. The stereoisomer is two or more compounds that differ in the spatial arrangement of the atoms. The resonance proceeds through delocalization of π-electrons present in the aromatic ring and they provide stability to the structure.

Interpretation Introduction

(e)

Interpretation:

An explanation as to the fact “Diazotization of 2,4- cyclopentadien -1- amine gives a diazonium salt, which unlike most aliphatic diazonium ions, is relatively stable and does not decompose to a carbocation” is to be stated.

Concept introduction:

The formation of diazonium salt from aromatic amines takes place using sodium nitrite and hydrochloric acid at low temperatures. This process is known as diazotization. The diazonium salts can be converted to aryl halides using copper halides or aryl cyanides using copper cyanides.

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Students have asked these similar questions
(a) Give a plausible explanation for each one of the following :(i) There are two – NH2 groups in semicarbazide. However, only one such group is involved in the formation of semicarbazones.(ii) Cyclohexanone forms cyanohydrin in good yield but 2, 4, 6-trimethylcyclohexanone does not.(b) An organic compound with molecular formula C9H10O forms 2, 4, – DNP derivative, reduces Tollens’ reagent and undergoes Cannizzaro’s reaction. On vigorous oxidation it gives 1, 2-benzene-di- carboxylic acid. Identify the compound.
(a) How will you convert:(i) Benzene to acetophenone                 (ii) Propanone to 2-Methylpropan-2-ol(b) Give reasons :(i) Electrophilic substitution in benzoic acid takes place at meta position.(ii) Carboxylic acids are higher boiling liquids than aldehydes, ketones and alcohols of comparable molecular masses.(iii) Propanal is more reactive than propanone in nucleophilic addition reactions.
Give reasons:  (i) Bond length of C = O in carboxylic acids is slightly larger than C = O bond length in carbonyl compounds.  (ii) There are two –NH2 groups in semicarbazide. However, only one –NH2 group is involved in the formation of semicarbazones.  (iii) Benzoic acid is less soluble in water than acetic acid. (iv) Formic acid is a stronger acid than acetic acid.

Chapter 23 Solutions

Organic Chemistry

Ch. 23 - Prob. 23.11PCh. 23 - Prob. 23.12PCh. 23 - Prob. 23.13PCh. 23 - Prob. 23.14PCh. 23 - Prob. 23.15PCh. 23 - Prob. 23.16PCh. 23 - Prob. 23.17PCh. 23 - Prob. 23.18PCh. 23 - Prob. 23.19PCh. 23 - Prob. 23.20PCh. 23 - Prob. 23.21PCh. 23 - Prob. 23.22PCh. 23 - Prob. 23.23PCh. 23 - Prob. 23.24PCh. 23 - Prob. 23.25PCh. 23 - Prob. 23.26PCh. 23 - Prob. 23.27PCh. 23 - Prob. 23.28PCh. 23 - Prob. 23.29PCh. 23 - Prob. 23.30PCh. 23 - Prob. 23.31PCh. 23 - Prob. 23.32PCh. 23 - Prob. 23.33PCh. 23 - Prob. 23.34PCh. 23 - Prob. 23.35PCh. 23 - Prob. 23.36PCh. 23 - Prob. 23.37PCh. 23 - Prob. 23.38PCh. 23 - Prob. 23.39PCh. 23 - Prob. 23.40PCh. 23 - Prob. 23.41PCh. 23 - Prob. 23.42PCh. 23 - Prob. 23.43PCh. 23 - Prob. 23.44APCh. 23 - Prob. 23.45APCh. 23 - Prob. 23.46APCh. 23 - Prob. 23.47APCh. 23 - Prob. 23.48APCh. 23 - Prob. 23.49APCh. 23 - Prob. 23.50APCh. 23 - Prob. 23.51APCh. 23 - Prob. 23.52APCh. 23 - Prob. 23.53APCh. 23 - Prob. 23.54APCh. 23 - Prob. 23.55APCh. 23 - Prob. 23.56APCh. 23 - Prob. 23.57APCh. 23 - Prob. 23.58APCh. 23 - Prob. 23.59APCh. 23 - Prob. 23.60APCh. 23 - Prob. 23.61APCh. 23 - Prob. 23.62APCh. 23 - Prob. 23.63APCh. 23 - Prob. 23.64APCh. 23 - Prob. 23.65APCh. 23 - Prob. 23.66APCh. 23 - Prob. 23.67APCh. 23 - Prob. 23.68APCh. 23 - Prob. 23.69APCh. 23 - Prob. 23.70APCh. 23 - Prob. 23.71APCh. 23 - Prob. 23.72APCh. 23 - Prob. 23.73APCh. 23 - Prob. 23.74APCh. 23 - Prob. 23.75APCh. 23 - Prob. 23.76APCh. 23 - Prob. 23.77APCh. 23 - Prob. 23.78APCh. 23 - Prob. 23.79APCh. 23 - Prob. 23.80APCh. 23 - Prob. 23.81AP
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